Consider a directed graph whose nodes are positive integers. There is a directed edge from $a$ to $b$ if $a<b$ and $a$ is relatively prime to $b$, i.e. $\mathrm{gcd}(a,b)=1$. Given two integers $x,y$ with $x<y$, $d(x,y)$ is the number of edges in the shortest path from $x$ to $y$. What is the largest value of $d(x,y)$?
I suspect the answer is 3, but I don't have a proof.
via Puzzle Tweeter
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Proof: For $y \leq 7$, this is easily checked. Otherwise by Bertrand's postulate, there is a prime $p$ with $x \leq \lceil y/2\rceil < p < y$. Now $\gcd(x,p) = \gcd(p,y) = 1$, so $d(x,y) \leq 2$.
By the last statement, we may assume $y < 2x$. Let $p$ be prime with $x \leq p \leq y$. Then $\gcd(x,p) = 1$, and because of $y < 2p$ also $\gcd(p,y) = 1$.
I used this property for a computer search for pairs $(x,y)$ with $d(x,y) > 2$. They turn out to be quite rare. The smallest ones are
In each such pair, $d(x,y) = 3$ and interestingly $y - x = 16$.